I am interested in selling some fonts I have made on my site and I am looking for the best recommendation on what I need to do to achieve the following.

The font I am selling has several different weights / styles and I'd like to be able to offer it as a 'full family' as well as giving customers the option to choose to purchase individual weights / styles of the font without having to purchase the entire font family.

My main questions are, how would I do this? I'd like the full family and the individual weights to be able to be purchased individually in a single product page.

I have read a little about grouped products, chained products and variable products, but I'm not sure which of these scenarios what I am trying to do would fall into.

I am effectively looking for there to be an add to cart button next to each scenario on the product page:

Your example has an image alongside each add to cart button, so the customer can very clearly see what they are getting. WooCommerce does not provide the facility to put an image adjacent to the quantity select dropdown, only a product title. The images would have to go a bit lower down the page in the product description. Also the product title links to the individual product page which can have its own image. So OK, but not as good. A compromise of using free software instead of bespoke software.

It might be possible with a plugin, though I don't know of any, or a custom development which would be outside the scope of this forum.